Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 4, Problem 40P
Interpretation Introduction
Interpretation:
The structures of the two compounds of molecular formula
Concept introduction:
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Compounds X and Y are stereoisomers having the formula C6H12.Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form hexane, and they each react with HBr to give a single bromoalkane product.Draw structural formulas for both X and Y.
sketch the various conformational isomers of 1,3-dimethylcyclohexane. Indicate the position (axial/equatorial) of each of the methyl groups in each structure.
Calculate the number of degrees of unsaturation for each molecular formula, and propose two possible structures: (a) C8H12; (b) C10H10.
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
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- The tsetse fly Glossina morsitans is a large biting fly foundin regions of Africa. They carry sleeping sickness, a deadlydisease caused by a parasitic protozoan. The pheromonesecreted by the tsetse fly contains four straight-chain alkanes:2-methylheptadecane (C18H38), 17,21-dimethylheptatriacontane (C39H80), 15,19-dimethylheptatriacontane (C39H80), and15,19,23-trimethylheptatriacontane (C40H82). Because thispheromone works by smell over long distances, it has proveduseful as an agent to control tsetse fly populations.a. Draw the line formula for each of these alkanes.b. Calculate the molar mass of each of these alkanes.arrow_forwardWrite a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.arrow_forward21.) Calculate the enthalpy of hydrogenation of benzene to cyclohexane from the following reactions A,H (kJ/mol) C6H6 (1) + 15/2 02 (g) → 6 CO2 (g) + 3 H20 (1) C6H12 (1) + 9 02 (g) → 6 CO2 (g) + 6 H20 (1) H2 (g) + ½ 02 (g) → H2O (1) -3268 -3920 -285.83 a.) -205 kJ/mol b.) -1507 kJ/mol c.) -938 kJ/mol d.) -366 kJ/molarrow_forward
- View and analyze the given spectroscopic data of an unknown compound with molecular formula C8H10O. Propose a structure based on your analysis. Support your answer by interpreting the given spectroscopic data.arrow_forwardExplain conformational analysis of cyclohexane.arrow_forwardDraw and name the six isomeric cyclopentane of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forward
- Compounds X and Y both have the formula C7H₁4. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylhexane. The heat of hydrogenation of X is greater than that of Y. Both X and Y react with HCI to give the same single C7H15Cl compound as the major product. What is the structure of X? • In cases where there is more than one answer, just draw one. 23 ▾ Sn [F ChemDoodleⓇ 146arrow_forwardTreatment of cyclohexene with C6H5CHI2 and Zn(Cu) forms two stereoisomers of molecular formula C13H16. Draw their structures and explain why two compounds are formed.arrow_forwardOne mole of an unknown hydrocarbon, compound C, in the presence of a platinum catalyst, adds 98.9 L of hydrogen, measured at 744 mm Hg and 22 degrees C , to form a saturated alkane which contains one ring. When one mole of compound C is reacted with ozone, followed by reduction with (CH3)2S , four moles of only one product was formed, whose condensed molecular formula is CHO -CHO. Give the structure of compound C. Explain your reasoningarrow_forward
- Choose the correct answer. Choose. Choose. An alkyne with molecular formula C5H10 A ketone with molecular formula C4H80 An aldehyde with molecular formula C2H4O A saturated hydrocarbon with molecular formula C6H14 An alkene with molecular formula C5H10 An alkene with molecular formula C5H8 A ketone with molecular formula C3H8O An aldehyde with molecular formula CH40 Choose.arrow_forwardDraw six isomeric cyclopentanes of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forwardA molecule with the molecular formula of C7H3O has a UV absorption of 282 nm. The IR spectrum of the molecule has absorbances at 3400 (broad), 1600, 1505, and 834 cm-¹. Draw a structure that best fits this data. Drawingarrow_forward
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